CN102174041A - High-purity silymarin and preparation method thereof - Google Patents
High-purity silymarin and preparation method thereof Download PDFInfo
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- CN102174041A CN102174041A CN2011100715087A CN201110071508A CN102174041A CN 102174041 A CN102174041 A CN 102174041A CN 2011100715087 A CN2011100715087 A CN 2011100715087A CN 201110071508 A CN201110071508 A CN 201110071508A CN 102174041 A CN102174041 A CN 102174041A
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Abstract
The invention discloses a high-purity silymarin and a preparation method thereof. The content of the high-purity silymarin is 97-101%. The preparation method of the high-purity silymarin comprises the following steps of: taking a silymarin shell as a raw material; adding ethyl acetate for dissolving the silymarin shell; extracting total flavones; collecting flavones in vacuum; and dissolving, extracting, filtering and drying the total flavones to obtain the high-purity silymarin. The invention has the advantages that on the basis of a silymarin seed, shell and kernel separating technology, the silymarin shell is used as the raw material for preparing the silymarin, the total flavones are extracted and then separated and purified by using ethanol with different concentration, and a recrystallization technology is adopted to prepare the high-purity silymarin. Because 99% of silymarin oil exists in the silymarin kernel, the silymarin shell is used for extracting the total flavones, the grease is little, a traditional method in which gasoline, petroleum ether and other organic solvents are used for degreasing is not required, and impurity interference, separation and purification difficulty and environment pollution are reduced. The preparation method disclosed by the invention is relatively simple, and the product quality and yield of the high-purity silymarin are greatly improved.
Description
Technical field
The present invention relates to a kind of silibinin and preparation method thereof, particularly a kind of high purity silibinin and preparation method thereof.
Background technology
Silibinin, chemical name: 2 α-［ 2,3-trans-2,3-dihydro-3-(4-hydroxy 3-methoxybenzene base)-and 2-methylol-1,4-benzodioxane-6-yl ］-2,3-dihydro-3 β, 5,7-trihydroxy--4H-1-chromene-4-ketone-hydrate, molecular formula: C
25H
22O
10H
2O, molecular weight: 500.47.
Silibinin is usually as bulk drug, is the effect that series product that raw material is made have liver protecting, repair liver plasma membrane with the silibinin, and this series products determined curative effect of clinical proof through for many years finds no any toxic side effect so far.Along with deepening continuously of research, the more more important activity of silibinin is progressively revealed, modern study proves that the high purity silibinin not only has liver protection function, also has effects such as anti-oxidant, radioprotective, anti-gastric-ulcer, antitumor and prevent diabetes complication.
The activeconstituents of silibinin for continue to use for many years always, it derives from silybum marianum seed, and the silibinin more than 99% is distributed in the shell in the silybum marianum seed.Because shell, the benevolence isolation technique of silybum marianum seed are still the technical barrier that is difficult to realize so far, still can only adopt traditional extracting effective components from the grouts after the full seed squeezing of silybum marianum seed so prepare the method for silibinin, the later separation purification difficult of this traditional method, the silibinin content that is prepared into is generally about 96%, can not break through 98% all the time.The high purity silibinin can only obtain in the laboratory on a small quantity, and its content is higher than the silibinin that traditional technology is produced far away, costs an arm and a leg.
Summary of the invention
Goal of the invention:, the purpose of this invention is to provide a kind of high purity silibinin at the problems referred to above.
Another object of the present invention provides a kind of high purity silibinin preparation method, and this preparation method is simple, has solved degreasing difficulty, separation and purification problem of difficult among traditional silibinin preparation method, has improved the silibinin content that makes.
Technical scheme: a kind of high purity silibinin, described high purity silibinin quality percentage composition is 97%～101%.
Described high purity silibinin content is to detect the quality percentage composition that draws with the HPLC method, with dry product.Detect product silibinin content of the present invention with the HPLC method, specificity is strong, detect product content more accurate,
A kind of preparation method of high purity silibinin, this method may further comprise the steps:
(1) be starting material with the Silymarin shell, add vinyl acetic monomer with the dissolving of Silymarin shell, extract total flavones, vacuum is received ketone; The mass ratio of described Silymarin shell and described vinyl acetic monomer is 1: 3～1: 3.2;
(2) total flavones may further comprise the steps through dissolving, extract, filter, be drying to obtain described high purity silibinin:
(A) after total flavones was dissolved in water, taking precipitate added ethanolic soln, dissolve silibinin crude product I;
(B) get silibinin crude product I and add ethanolic soln, dissolving back crystallization gets silibinin crude product II;
(C) get silibinin crude product II and add dehydrated alcohol, dissolving back millipore filtration, filtrate is concentrated into silibinin crude product II and adding dehydrated alcohol cumulative volume 20%～30%, crystallization, filter, be drying to obtain described high purity silibinin.
The extraction of the adding of vinyl acetic monomer and total flavones is all successively carried out at twice in the step (1), and the Silymarin shell that adds in the time of for the first time and the mass ratio of vinyl acetic monomer are 1: 1.7～1: 1.8, extracts total flavones 2 hours; The Silymarin shell that adds in the time of for the second time and the mass ratio of vinyl acetic monomer are 1: 1.3～1: 1.4, extract total flavones 16～18 hours.
Extract for the first time total flavones, extraction equipment adopts self-circulation mode; Extract for the second time total flavones, extraction equipment adopts the systemic circulation mode; Self-circulation, systemic circulation be every 20～30 minutes circulation primary, each 10～15 minutes.
The temperature of receiving ketone in the step (1) is 91 ℃～92 ℃.
As the process pulverizing earlier of raw-material Silymarin shell, be beneficial to dissolving and extract total flavones in the step (1).
The concentration of ethanolic soln is 50% in the step (A), and the concentration of ethanolic soln is 65% in the step (B); More than be the quality percentage composition.
The add-on of the middle ethanolic soln of step (A) is 3 times of described total flavones quality, the add-on of the middle ethanolic soln of step (B) is 3 times of described silibinin crude product I quality, and the add-on of the middle dehydrated alcohol of step (C) is 10～12 times of described silibinin crude product II quality.
Beneficial effect: compared with prior art, advantage of the present invention is: 1, based on silybum marianum seed shell benevolence isolation technique, with the raw material of Silymarin shell as the preparation silibinin, extract total flavones, use the Different concentrations of alcohol separation and purification again, and adopt recrystallization technology to make the high purity silibinin, the UV method detect silibinin content 〉=99%, the HPLC method detect silibinin content 〉=97%, all above state-set standard; 2, be present in the Silymarin benevolence owing to Silymarin oil 99%, therefore extract total flavones with the Silymarin shell, grease seldom, the organic solvent such as use gasoline, sherwood oil that need not in the traditional method carries out degreasing, reduce impurity and disturb and separation and purification difficulty and environmental pollution, vinyl acetic monomer can be removed minute quantity grease wherein in dissolving Silymarin shell in the inventive method; 3, preparation method of the present invention is simple relatively, is applicable to industrial mass production, and high purity silibinin quality product and yield improve greatly, and production capacity has increased by one times than traditional method.
Embodiment
Below in conjunction with specific embodiment, further illustrate the present invention, should understand these embodiment only is used to the present invention is described and is not used in and limit the scope of the invention, after having read the present invention, those skilled in the art all fall within the application's claims institute restricted portion to the modification of the various equivalent form of values of the present invention.
Embodiment 1: get the Silymarin shell meal of 600g after 16 orders are pulverized and feed intake, adding the 1020g vinyl acetic monomer dissolves it, refluxing extraction total flavones 2 hours, and then adding 780g vinyl acetic monomer, refluxing extraction total flavones 16 hours, the total flavones liquid that merges extracted twice, vacuum is received ketone and is got the 82g total flavones.
The purified water that is incorporated as 5 times of amounts of total flavones quality stirs the dissolving of 82g total flavones water-bath and puts calm putting 1 hour, and it is that 50% ethanolic soln dissolves it that taking precipitate adds 246g concentration, obtains silibinin crude product I 70g; Adding 210g concentration is 65% dissolve with ethanol solution in silibinin crude product I, and crystallization obtained silibinin crude product II 52g in 24 hours; In silibinin crude product II, add the 520g anhydrous alcohol solution, after treating to dissolve fully, millipore filtration while hot, filtrate is concentrated into silibinin crude product II and adding dehydrated alcohol cumulative volume about 20%, room temperature is placed 22 hours crystallizatioies, filtration, get filter cake and obtain high purity silibinin 8.4g in 80 ℃ of vacuum-dryings, it is 99.6% that the HPLC method records its content.
Embodiment 2: get 600g Silymarin shell and feed intake, add the 1020g vinyl acetic monomer and it is dissolved refluxing extraction total flavones 2 hours, and then adding 780g vinyl acetic monomer, refluxing extraction total flavones 16 hours, the total flavones liquid of merging extracted twice, vacuum is received ketone and is got the 78g total flavones.
The purified water that is incorporated as 5 times of amounts of total flavones quality stirs the dissolving of 78g total flavones water-bath and puts calm putting 1 hour, and it is that 50% ethanolic soln dissolves it that taking precipitate adds 234g concentration, obtains silibinin crude product I 65g; Adding 210g concentration is 65% dissolve with ethanol solution in silibinin crude product I, and crystallization obtained silibinin crude product II 48g in 24 hours; In silibinin crude product II, add the 480g anhydrous alcohol solution, after treating to dissolve fully, millipore filtration while hot, filtrate is concentrated into silibinin crude product II and adding dehydrated alcohol cumulative volume about 20%, room temperature is placed 22 hours crystallizatioies, filtration, get filter cake and obtain high purity silibinin 7.8g in 80 ℃ of vacuum-dryings, it is 99.2% that the HPLC method records its content.
Embodiment 3: get the Silymarin shell meal of 300g after 16 orders are pulverized and feed intake, adding the 510g vinyl acetic monomer dissolves it, refluxing extraction total flavones 2 hours, and then adding 390g vinyl acetic monomer, refluxing extraction total flavones 16 hours, the total flavones liquid that merges extracted twice, vacuum is received ketone and is got the 45g total flavones.
The purified water that is incorporated as 3 times of amounts of total flavones quality stirs the dissolving of 45g total flavones water-bath and puts calm putting 1 hour, and it is that 50% ethanolic soln dissolves it that taking precipitate adds 135g concentration, obtains silibinin crude product I 34g; Adding 102g concentration is 65% dissolve with ethanol solution in silibinin crude product I, and crystallization obtained silibinin crude product II 25g in 24 hours; In silibinin crude product II, add the 250g anhydrous alcohol solution, after treating to dissolve fully, millipore filtration while hot, filtrate is concentrated into silibinin crude product II and adding dehydrated alcohol cumulative volume about 20%, room temperature is placed 22 hours crystallizatioies, filtration, get filter cake and obtain high purity silibinin 3.8g in 80 ℃ of vacuum-dryings, it is 98.5% that the HPLC method records its content.
A kind of high purity silibinin of the present invention and preparation method thereof, be to be based upon on the basis of silybum marianum seed shell benevolence isolation technique, particularly for industrialization, scale operation, the effective silybum marianum seed shell benevolence separating device by developing at first obtains the Silymarin shell.
Table 1:
| Extract material | The Silymarin shell | Silymarin benevolence |
| Charging capacity | 300g | 300g |
| Silibinin | 26.7g | Do not have |
| The silibinin yield | 8.9% | ? |
| Silibinin content (HPLC) | 98.28% | ? |
Table 1 column data is for extracting the yield and the content of silibinin respectively, as seen: can not extract silibinin in the Silymarin benevolence, prove that further the silibinin in the silybum marianum seed is present in the Silymarin shell with Silymarin shell and Silymarin benevolence.
Adopt the Silymarin shell to extract silibinin, the consumption of vinyl acetic monomer is than adopting silybum marianum seed to extract silibinin in theory, and extraction material per ton on average reduces the about 20kg of vinyl acetic monomer consumption, saves cost, reduces the influence to environment simultaneously.
Table 2:
Table 2 column data, for adopting the 1000g silybum marianum seed respectively is the Silymarin shell and the Silymarin cake of charging capacity in the raw material acquisition table, adopt same extracting method and extraction time, silybum marianum seed with the different places of production, squeeze yield and the content that the Silymarin cake that forms extracts silibinin respectively with its Silymarin shell with by the full seed of silybum marianum seed, as seen: the silybum marianum seed in the same place of production, though attribute composition unanimity, the yield of the silibinin that extracts with the Silymarin shell and content all are higher than the yield and the content of the silibinin that the Silymarin cake that formed by the full seed squeezing of silybum marianum seed extracts.
Table 3:
Table 3 column data, for using Silymarin shell of not pulverizing and yield and the content that extracts silibinin through the Silymarin shell that 16 orders are pulverized respectively, as seen: extract the yield of silibinin about 10 ‰ with the Silymarin shell of not pulverizing, and use the Silymarin shell of pulverizing through 16 orders to extract the yield of silibinin about 12 ‰, two kinds of content difference of extracting the silibinin that material obtains are few, illustrate that the Silymarin shell is ground into meal and more helps extracting silibinin.
Table 4:
| The volume ratio of filtrate concentrated solution | 22 hours crystallization amounts | Silibinin content (HPLC) |
| 50% | 0.62g | 100.2% |
| 40% | 0.84g | 100.0% |
| 30% | 1.26g | 99.8% |
| 20% | 1.68g | 99.6% |
| 10% | 2.12g | 92.7% |
Table 4 column data, for with the silibinin crude product II 52g among the embodiment 1, filtrate behind the adding 520g anhydrous alcohol solution, be divided into five parts, the content of the silibinin that concentrates under different parameters, obtains behind the crystallization relatively, " volume ratio of filtrate concentrated solution " is meant the volume and the ratio of silibinin crude product II with the cumulative volume of the dehydrated alcohol of adding after filtrate concentrates in the table, as seen: in the filtrate after concentrating, the speed that how much has influence on crystallization of amount of alcohol, amount of alcohol is big, silibinin is difficult for crystallization, crystallization speed is slow, but silibinin purity height; Amount of alcohol is very few, and the easy crystallization of silibinin, crystallization speed are fast, but silibinin purity does not reach high purity.Therefore, take all factors into consideration, the volume ratio 20%～30% of selecting the filtrate concentrated solution is best.
Claims (9)
1. high purity silibinin, it is characterized in that: described high purity silibinin quality percentage composition is 97%～101%.
2. a kind of high purity silibinin according to claim 1 is characterized in that: described high purity silibinin content is to detect the quality percentage composition that draws with the HPLC method, with dry product.
3. the preparation method of a kind of high purity silibinin according to claim 1 is characterized in that this method may further comprise the steps:
(1) be starting material with the Silymarin shell, add vinyl acetic monomer with the dissolving of Silymarin shell, extract total flavones, vacuum is received ketone; The mass ratio of described Silymarin shell and described vinyl acetic monomer is 1: 3～1: 3.2;
(2) total flavones may further comprise the steps through dissolving, extract, filter, be drying to obtain described high purity silibinin:
(A) after total flavones was dissolved in water, taking precipitate added ethanolic soln, dissolve silibinin crude product I;
(B) get silibinin crude product I and add ethanolic soln, dissolving back crystallization gets silibinin crude product II;
(C) get silibinin crude product II and add dehydrated alcohol, dissolving back millipore filtration, filtrate is concentrated into silibinin crude product II and adding dehydrated alcohol cumulative volume 20%～30%, crystallization, filter, be drying to obtain described high purity silibinin.
4. the preparation method of a kind of high purity silibinin according to claim 3, it is characterized in that: the extraction of the adding of vinyl acetic monomer and total flavones is all successively carried out at twice in the step (1), the Silymarin shell that adds in the time of for the first time and the mass ratio of vinyl acetic monomer are 1: 1.7～1: 1.8, extract total flavones 2 hours; The Silymarin shell that adds in the time of for the second time and the mass ratio of vinyl acetic monomer are 1: 1.3～1: 1.4, extract total flavones 16～18 hours.
5. the preparation method of a kind of high purity silibinin according to claim 4 is characterized in that: extract total flavones for the first time, extraction equipment adopts self-circulation mode; Extract for the second time total flavones, extraction equipment adopts the systemic circulation mode; Self-circulation, systemic circulation be every 20～30 minutes circulation primary, each 10～15 minutes.
6. the preparation method of a kind of high purity silibinin according to claim 3 is characterized in that: the temperature of receiving ketone in the step (1) is 91 ℃～92 ℃.
7. the preparation method of a kind of high purity silibinin according to claim 3 is characterized in that: first through pulverizing as raw-material Silymarin shell in the step (1).
8. the preparation method of a kind of high purity silibinin according to claim 3 is characterized in that: the concentration of ethanolic soln is 50% in the step (A), and the concentration of ethanolic soln is 65% in the step (B); More than be the quality percentage composition.
9. the preparation method of a kind of high purity silibinin according to claim 3, it is characterized in that: the add-on of the middle ethanolic soln of step (A) is 3 times of described total flavones quality, the add-on of the middle ethanolic soln of step (B) is 3 times of described silibinin crude product I quality, and the add-on of the middle dehydrated alcohol of step (C) is 10～12 times of described silibinin crude product II quality.
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| CN103408539A (en) * | 2013-08-28 | 2013-11-27 | 天津泰阳制药有限公司 | Production method of high-purity silibinin |
| CN104710414A (en) * | 2013-12-13 | 2015-06-17 | 中国科学院大连化学物理研究所 | Preparation method of 2,3-cis-silybin B |
| WO2015197854A1 (en) * | 2014-06-26 | 2015-12-30 | Bionorica Se | Milk thistle extract from the fruit peels of milk thistle, method for production and use thereof |
| CN105622594A (en) * | 2016-03-17 | 2016-06-01 | 江苏中兴药业有限公司 | Method for preparing high-purity silymarin |
| CN105693708A (en) * | 2014-11-25 | 2016-06-22 | 河南智晶生物科技股份有限公司 | Silymarin extraction method |
| CN105884754A (en) * | 2016-05-17 | 2016-08-24 | 江苏健佳药业有限公司 | Fine extraction method of silibinin |
| CN106083834A (en) * | 2016-06-21 | 2016-11-09 | 江苏中兴药业有限公司 | A kind of high-purity silymarin isolation and purification method |
| CN107098892A (en) * | 2017-06-07 | 2017-08-29 | 江苏天晟药业股份有限公司 | A kind of method of purification of legalon |
| CN107260787A (en) * | 2017-08-09 | 2017-10-20 | 江苏中兴药业有限公司 | A kind of method for improving milk thistle shell effective ingredient dissolution |
| CN107793402A (en) * | 2017-09-26 | 2018-03-13 | 江苏健佳药业有限公司 | A kind of extracting method of legalon |
| CN108456199A (en) * | 2017-02-20 | 2018-08-28 | 南京宸翔医药研究有限责任公司 | A kind of production technology, pharmaceutical composition and its clinical application of high-purity silymarin meglumine |
| CN108640908A (en) * | 2018-07-16 | 2018-10-12 | 武汉轻工大学 | The silibinin and preparation method thereof of high-purity low solvent residue |
| CN109438428A (en) * | 2018-10-18 | 2019-03-08 | 江苏中兴药业有限公司 | A kind of circulating isolation and purification method of silibinin |
| CN110878093A (en) * | 2019-12-18 | 2020-03-13 | 湖南千金协力药业有限公司 | Preparation method of high-purity silybin |
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| CN103408539A (en) * | 2013-08-28 | 2013-11-27 | 天津泰阳制药有限公司 | Production method of high-purity silibinin |
| CN104710414A (en) * | 2013-12-13 | 2015-06-17 | 中国科学院大连化学物理研究所 | Preparation method of 2,3-cis-silybin B |
| WO2015197854A1 (en) * | 2014-06-26 | 2015-12-30 | Bionorica Se | Milk thistle extract from the fruit peels of milk thistle, method for production and use thereof |
| EP2959910A1 (en) * | 2014-06-26 | 2015-12-30 | Bionorica Se | Milk thistle extract of fruit shells of Silybum marianum, process of manufacture and use |
| CN105693708A (en) * | 2014-11-25 | 2016-06-22 | 河南智晶生物科技股份有限公司 | Silymarin extraction method |
| CN105622594B (en) * | 2016-03-17 | 2019-05-17 | 江苏中兴药业有限公司 | A kind of preparation method of high-purity silymarin |
| CN105622594A (en) * | 2016-03-17 | 2016-06-01 | 江苏中兴药业有限公司 | Method for preparing high-purity silymarin |
| CN105884754A (en) * | 2016-05-17 | 2016-08-24 | 江苏健佳药业有限公司 | Fine extraction method of silibinin |
| CN106083834A (en) * | 2016-06-21 | 2016-11-09 | 江苏中兴药业有限公司 | A kind of high-purity silymarin isolation and purification method |
| CN106083834B (en) * | 2016-06-21 | 2018-07-17 | 江苏中兴药业有限公司 | A kind of silibinin isolation and purification method |
| CN108456199A (en) * | 2017-02-20 | 2018-08-28 | 南京宸翔医药研究有限责任公司 | A kind of production technology, pharmaceutical composition and its clinical application of high-purity silymarin meglumine |
| CN107098892A (en) * | 2017-06-07 | 2017-08-29 | 江苏天晟药业股份有限公司 | A kind of method of purification of legalon |
| CN107260787A (en) * | 2017-08-09 | 2017-10-20 | 江苏中兴药业有限公司 | A kind of method for improving milk thistle shell effective ingredient dissolution |
| CN107260787B (en) * | 2017-08-09 | 2020-07-21 | 江苏中兴药业有限公司 | Method for improving dissolution of effective components of silybum marianum shells |
| CN107793402A (en) * | 2017-09-26 | 2018-03-13 | 江苏健佳药业有限公司 | A kind of extracting method of legalon |
| CN108640908A (en) * | 2018-07-16 | 2018-10-12 | 武汉轻工大学 | The silibinin and preparation method thereof of high-purity low solvent residue |
| CN109438428A (en) * | 2018-10-18 | 2019-03-08 | 江苏中兴药业有限公司 | A kind of circulating isolation and purification method of silibinin |
| CN110878093A (en) * | 2019-12-18 | 2020-03-13 | 湖南千金协力药业有限公司 | Preparation method of high-purity silybin |
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